US4134929A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Allyl 2-cyanoacrylate-based orthodontic bracket adhesive
Assignee: Permabond International Corp
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Filing: 1976-07-23
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Granted: 1979-01-16
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Expires: 1996-07-23
Abstract
Abstract An adhesive composition comprising Components A, B and C as follows: A. a polymerizable monomeric allyl 2-cyanoacrylate containing portion comprising 1. from about 75 to about 92 parts by weight of allyl 2-cyanoacrylate; 2. from about 1 to about 12 parts by weight of a difunctional monomer diester of an acid from the group consisting of acrylic and methacrylic acid and an aromatic diol; and 3. from about 3 to 20 parts by weight of a thickening agent selected from poly(methylacrylate-coacrylonitrile) polymers; B. from 0.1 to 3.0 weight percent based upon the weight of component A of a hydrophobic cyclic imino initiator selected from 2,4,6-tri(allyloxy)-S-triazine, tri(alkyloxy)-S-triazines having 1 to about 20 exocyclic carbon atoms, benzoxazole and substituted benzoxazoles; and C. an amount of an organic peroxide free radical providing compound sufficient to cause cross linking of the difunctional monomer diester with the allyl 2-cyanoacrylate.
Inventors
- 👤 Diane M. Stoakley
- 👤 John R. Dombroski
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 08:16
CPC Classifications
C; C09; C09J; C09J4/00; C09J4/06
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
185 words
A solidified adhesive compound exhibiting hydrolytic stability which solidified adhesive compound results from combining components A, B and C as follows: A. a polymerizable monomeric allyl 2-cyanoacrylate containing portion prepared from 1. from 75 to about 92 parts by weight of allyl 2-cyanoacrylate; 2. from 1 to about 12 parts by weight of a difunctional monomer diester of an acid from the group consisting of acrylic and methacrylic acid and a diol having an aromatic nucleus; and 3. from 3 to about 20 parts by weight of a thickening agent selected from poly(methylacrylate-co-acrylonitrile) polymers; B. from 0.1 to about 3 weight percent based upon the weight of component A of a hydrophobic cyclic imino initiator selected from the group consisting of 2,4,6-tri(allyloxy)-S-triazine, tri(alkyloxy)-S-triazines having 1 to about 20 exocyclic carbon atoms; and benzoxazoles having the formula ##STR4## wherein each R is the same or different and represents hydrogen, phenyl, alkyl of 1 to about 20 carbon atoms, chloro or bromo; and C. an amount of an organic peroxide free radical providing compound sufficient to cause crosslinking of the difunctional monomer diester with the allyl 2-cyanoacrylate.
Claim 2
Dependent Claim
185 words
A solidified adhesive compound exhibiting hydrolytic stability which solidified adhesive compound results from combining components A, B and C as follows: A. a polymerizable monomeric allyl 2-cyanoacrylate containing portion prepared from 1. from 75 to about 92 parts by weight of allyl 2-cyanoacrylate; 2. from 1 to about 12 parts by weight of a difunctional monomer diester of an acid from the group consisting of acrylic and methacrylic acid and a diol having an aromatic nucleus; and 3. from 3 to about 20 parts by weight of a thickening agent selected from poly(methylacrylate-co-acrylonitrile) polymers; B. from 0.1 to about 3 weight percent based upon the weight of component A of a hydrophobic cyclic imino initiator selected from the group consisting of 2,4,6-tri(allyloxy)-S-triazine, tri(alkyloxy)-S-triazines having 1 to about 20 exocyclic carbon atoms; and benzoxazoles having the formula ##STR4## wherein each R is the same or different and represents hydrogen, phenyl, alkyl of 1 to about 20 carbon atoms, chloro or bromo; and C. an amount of an organic peroxide free radical providing compound sufficient to cause crosslinking of the difunctional monomer diester with the allyl 2-cyanoacrylate.
Claim 3
Dependent Claim
156 words
A solidified adhesive compound exhibiting hydrolytic stability which solidified adhesive compound results from combining components A, B and C as follows: A. a polymerizable monomeric allyl 2-cyanoacrylate containing portion prepared from 1. from 75 to about 92 parts by weight of allyl 2-cyanoacrylate; 2. from 1 to about 12 parts by weight of a difunctional monomer diester of an acid from the group consisting of acrylic and methacrylic acid an a diol having an aromatic nucleus; and 3. from 3 to about 20 parts by weight of a thickening agent selected from poly(methylacrylate-co-acrylonitrile) polymers; B. from 0.1 to about 3.0 weight percent based upon the weight of component A of a cyclic imino initiator selected from the group consisting of 2,4,6-tri(allyloxy)-S-triazine and tri(alkyloxy)-S-triazines having 1 to about 20 exocyclic carbon atoms; and C. an amount of an organic peroxide free radical providing compound sufficient to cause crosslinking of the difunctional monomer diester with the allyl 2-cyanoacrylate.
Claim 4
Dependent Claim
156 words
A solidified adhesive compound exhibiting hydrolytic stability which solidified adhesive compound results from combining components A, B and C as follows: A. a polymerizable monomeric allyl 2-cyanoacrylate containing portion prepared from 1. from 75 to about 92 parts by weight of allyl 2-cyanoacrylate; 2. from 1 to about 12 parts by weight of a difunctional monomer diester of an acid from the group consisting of acrylic and methacrylic acid an a diol having an aromatic nucleus; and 3. from 3 to about 20 parts by weight of a thickening agent selected from poly(methylacrylate-co-acrylonitrile) polymers; B. from 0.1 to about 3.0 weight percent based upon the weight of component A of a cyclic imino initiator selected from the group consisting of 2,4,6-tri(allyloxy)-S-triazine and tri(alkyloxy)-S-triazines having 1 to about 20 exocyclic carbon atoms; and C. an amount of an organic peroxide free radical providing compound sufficient to cause crosslinking of the difunctional monomer diester with the allyl 2-cyanoacrylate.
Claim 5
Dependent Claim
155 words
A solidified adhesive compound exhibiting hydrolytic stability which solidified adhesive compound results from combining components A, B and C as follows: A. a polymerizable monomeric allyl 2-cyanoacrylate containing portion prepared from 1. from 83 to 91 parts by weight of allyl 2-cyanoacrylate; 2. from 1 to about 8 parts by weight of a difunctional monomer diester of an acid from the group consisting of acrylic and methacrylic acid and a diol having an aromatic nucleus; and 3. from 7 to about 15 parts by weight of a thickening agent selected from poly(methylacrylate-co-acrylonitrile) polymers; B. from 0.3 to about 2.5 weight percent based upon the weight of component A of a cyclic imino initiator selected from the group consisting of 2,4,6-tri(allyloxy)-S-triazine and tri(alkyloxy)-S-triazines having 1 to about 20 exocyclic carbon atoms; and C. an amount of an organic peroxide free radical providing compound sufficient to cause crosslinking of the difunctional monomer diester with the allyl 2-cyanoacrylate.
Claim 6
Dependent Claim
155 words
A solidified adhesive compound exhibiting hydrolytic stability which solidified adhesive compound results from combining components A, B and C as follows: A. a polymerizable monomeric allyl 2-cyanoacrylate containing portion prepared from 1. from 83 to 91 parts by weight of allyl 2-cyanoacrylate; 2. from 1 to about 8 parts by weight of a difunctional monomer diester of an acid from the group consisting of acrylic and methacrylic acid and a diol having an aromatic nucleus; and 3. from 7 to about 15 parts by weight of a thickening agent selected from poly(methylacrylate-co-acrylonitrile) polymers; B. from 0.3 to about 2.5 weight percent based upon the weight of component A of a cyclic imino initiator selected from the group consisting of 2,4,6-tri(allyloxy)-S-triazine and tri(alkyloxy)-S-triazines having 1 to about 20 exocyclic carbon atoms; and C. an amount of an organic peroxide free radical providing compound sufficient to cause crosslinking of the difunctional monomer diester with the allyl 2-cyanoacrylate.
Claim 7
Dependent Claim
31 words
A solidified adhesive compound exhibiting hydrolytic stability which solidified adhesive compound results from combining components A, B and C as follows: A. a polymerizable monomeric allyl 2-cyanoacrylate containing portion prepared from
Claim 8
Dependent Claim
31 words
A solidified adhesive compound exhibiting hydrolytic stability which solidified adhesive compound results from combining components A, B and C as follows: A. a polymerizable monomeric allyl 2-cyanoacrylate containing portion prepared from
Claim 9
Dependent Claim
128 words
from 83 to about 91 parts by weight of allyl 2-cyanoacrylate; 2. from 1 to about 8 parts by weight of a difunctional monomer diester selected from the group consisting of bisphenol A dimethacrylate, bis(hydroxyethyl terephthalate), diacrylate, and p-xylylene glycol bisacrylate; 3. from 7 to about 15 parts by weight of a thickening agent selected from poly(methylacrylate-co-acrylonitrile) polymer derived from an 80/20 to 20/80 weight % ratio of the methyl acrylate to acrylonitrile comonomer; B. from 0.3 to about 2.5 weight percent based on the weight of component A of a cyclic imino initiator selected from the group consisting of 2,4,6-tri(allyloxy)-S-triazine and 2,4,6-tri(propoxy)-S-triazines; and C. an amount of an organic peroxide free radical providing compound sufficient to cause crosslinking of the difunctional monomer diester with the allyl 2-cyanoacrylates.
Claim 10
Dependent Claim
128 words
from 83 to about 91 parts by weight of allyl 2-cyanoacrylate; 2. from 1 to about 8 parts by weight of a difunctional monomer diester selected from the group consisting of bisphenol A dimethacrylate, bis(hydroxyethyl terephthalate), diacrylate, and p-xylylene glycol bisacrylate; 3. from 7 to about 15 parts by weight of a thickening agent selected from poly(methylacrylate-co-acrylonitrile) polymer derived from an 80/20 to 20/80 weight % ratio of the methyl acrylate to acrylonitrile comonomer; B. from 0.3 to about 2.5 weight percent based on the weight of component A of a cyclic imino initiator selected from the group consisting of 2,4,6-tri(allyloxy)-S-triazine and 2,4,6-tri(propoxy)-S-triazines; and C. an amount of an organic peroxide free radical providing compound sufficient to cause crosslinking of the difunctional monomer diester with the allyl 2-cyanoacrylates.
Claim 11
Dependent Claim
31 words
The composition of claim 4 wherein the difunctional monomer diester is bisphenol A dimethacrylate, the thickening agent is poly(60 wt. % methyl acrylate-co-40 wt. % acrylonitrile) and the initiator is 2,4,6-tri(n-propoxy)-S-triazine.
Claim 12
Dependent Claim
14 words
The composition of claim 5 wherein the free radical providing compound is benzoyl peroxide.
Claim 13
Dependent Claim
31 words
The composition of claim 4 wherein the difunctional monomer diester is bisphenol A dimethacrylate, the thickening agent is poly(60 wt. % methyl acrylate-co-40 wt. % acrylonitrile) and the initiator is 2,4,6-tri(allyloxy)-S-triazine.
Claim 14
Dependent Claim
14 words
The compositon of claim 7 wherein the free radical providing compound is benzoyl peroxide.
References Cited (Backward Citations)
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US3832334A
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-01-15 | 1982-07-17 | 1983-01-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-01-15 | 1986-07-17 | 1987-01-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-01-15 | 1990-07-17 | 1991-01-16 | $7700.00 | Window Closed / Lapsed |